00148 - CHIMICA ORGANICA

Academic Year 2022/2023

  • Moduli: Paola Galletti (Modulo 1) Chiara Samorì (Modulo 2)
  • Teaching Mode: Traditional lectures (Modulo 1) Traditional lectures (Modulo 2)
  • Campus: Ravenna
  • Corso: Single cycle degree programme (LMCU) in Conservation and restoration of cultural heritage (cod. 8616)

Learning outcomes

After learning, the student will have a basic knowlegde of structure, properties and reactivity of the main classes of organic compounds and of some natural organic products. The student will be able to: write and understand the structure of organic molecules; forecast the products and mechanism of simple organic reactions.

Course contents

Electronic structure and hybridation of the carbon atom. Covalent bonds in organic molecules; electronic resonance.

Functional groups, nomenclature and representation of organic compounds. Structure and conformations of alkanes. Ring strain and conformations of cycloalkanes.

Stereochemistry of organic molecules: chirality, configuration and representation of chiral molecules; enantiomery and diastereoisomery, brief survey on optical acivity.

Elementary reaction mechanisms. Acids and based. Electropiles, nucleophiles and radicals. Representation of organic chemical reactions. Brief survey of thermodynamics, kinetics and reaction energy plots.

Main classes of organic compounds and their reactions:

Alkanes, origin, physical properties; combustion. Radicalic halogenations of alkanes;

Haloalkanes, nucleophilic substitution, SN1, SN2, stereochemistry of SN; elimination reaction E1 and E2. Brief survey on organometallic compounds;

Alkenes, Structure and isomers of C=C bond. Electrophilic and radicalic addition to C=C double bond, addition of alogenhydric acids, water, alcohols, hydrogen. Oxidations of alkenes: epoxidation, ozonolysis, dihydrixylation. Radicalic polymerization, principal alkenylic polymers;

Alkynes, structure of the triple bond; electrophilic addition to alkynes, hydrogenantion and semihydrogenetion of alkynes. Acidity of alkynes and reactions of alkynyl anaions;

Conjugated dienes, elementary knowledge of electronic structure of conjugated dienes, electronic transitions and photons assorbtion; 1,2 and 1,4 additions to dienes, allylic resonance;

Alcohols, ethers and epoxides, hydrogen bonding, acidity of alcohols; alkylation of alkoxides; oxidation of alcohols; nucleophilic substitution on alcohols and ethers; nucleophilic addition to epoxides;

Carbonyl componuds, nucleophilic addition to carbonyls, addition of organimetallic compounds, hydrides, water, alcohols, amines; hydrogenation of carbonyls; oxidation of aldehydes. Enolization, keto-enol tautomery, aldol reaction;

Acylic compounds, carboxylic acids, acyl halides, anhydrides, esters, amides; acidity of carboxylic acids. Nucleophilic acylic substitution, reactivity scale of acylic compounds and their interconversion reactions; possibly, basics on nitrils;

Amines, basicity of amines; alkylation of amines, reductive amination of carbonyl compounds;

Aromatic compounds, concept of aromaticity; aromatic electrophilic substitution, halogenations, nitration, sulfonation, Friedel-Crafts reactions; possibly, introduction to substituent effects. Phenols and anilines; brief survey on heterocyclic compounds and aromatic polycyclic hydrocarbons;

Natural products, carbohydrates, structure, stereochemistry, nomenclature of monosaccarids; di- and polysaccarides: lipids, fatty acids and triglicerids, surfactants and detergents; aminoacids, structure and stereochemistry, proteinogenic aminoacids; peptidic bond, polypeptides and proteins.

Exercises about all topics above mentioned.

Readings/Bibliography

All Organic Chemistry textbooks at university level will be suitable.

Some exempilificative options

P. Vollahrdt “Chimica Organica”, Zanichelli, Bologna

P. J. Bruice “Chimica Organica”, EDISES, Napoli,

W. H . Brown, C. S. Foote, et al. “Chimica Organica”, EDISES, Napoli

J. McMurry “Fondamenti di Chimica Organica”, Zanichelli, Bologn

Teaching methods

Lectures and discussion
Exercises

Assessment methods

The exam will be oral and will deal with the whole program.

Questions will be asked on general topics then more specific topics will be explored. In addition, small exercises can be proposed on topics of nomenclature, stereochemistry, synthetic steps, selectivity.

Teaching tools

Power point slides.

Office hours

See the website of Paola Galletti

See the website of Chiara Samorì